Fashion Face-Off: Kendall Jenner vs. Kylie Jenner

Published on October 24, 2019. Updated December 1, 2022

When it comes to fashion, Kendall and Kylie Jenner definitely have different tastes! As a model, Kendall is quite experimental with her fashion and isn’t afraid to step out wearing something avant-garde and unique. Kylie is a little more simplistic with her style often favoring neutrals and clean lines. Kendall and Kylie are known for stepping out on the red carpet together, so follow along for our fashion-face off between the two famous sisters.

25. ICONS By Carine Roitfeld Celebration — 2016

In 2016, Kylie and Kendall stepped out together for the ICONS by Carine Roitfeld celebration at the Plaza Hotel in New York City. While Kylie wore a pink beaded mini dress with a blonde bob, Kendall wore a long floral embellished look with sheer detailing and tousled bangs. Whose look do you prefer? Be sure to vote below!

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24. Seventeen Magazine Event — 2012

Kendall and Kylie stepped out together in 2012 for a Seventeen Magazine event. For the occasion, Kendall opted for a white and teal dress which she paired with platform heels and a chunky necklace. Kylie opted for a white lace dress which she accessorized with a metallic belt and coordinating silver pumps. While Kendall styled her hair in a sleek topknot, Kylie opted for long loose waves. Whose look do you prefer?

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23. KIIS FM’s Jingle Ball – 2012

In 2012, the famous sisters stepped out in leather for the KIIS FM Jingle Ball event. Kylie wore a band tee paired with a skater-style leather skirt. She accessorized with simple black pumps and wore her long brunette hair sleek and straight. Kendall, on the other hand, wore a grey cutout shirt paired with a tight leather miniskirt. She opted for a high ponytail with her hair. Whose leather look do you prefer? Be sure to vote below!

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22. Teen Choice Awards – 2014

Kendall and Kylie definitely had different takes on their Teen Choice Awards outfits in 2014. Kendall looked very model-esque with her white drapey jumpsuit and slicked back tresses. Kylie looked chic and sweet in a black crop top and printed mini skirt. Whose Teen Choice awards look do you prefer?

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21. Annual Race To Erase MS — 2012

In 2012 Kylie and Kendall stepped out for the Annual Race to Erase MS event. While Kendall opted for a sequin mini dress with black platform heels, Kylie wore a black chiffon dress with a sheer skirt. Whose look do you prefer? Be sure to vote below!

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20. Wango Tango concert — 2013

For the Wango Tango concert in 2013, the famous sisters stepped out dressed quite casually. While Kendall wore leather leggings with a grey printed tank top, Kylie wore a black high-neck top and jeans which she dolled up with a red lip and coordinating red heels. Whose look do you prefer?

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19. Kardashian Kollection Launch Party – 2011

Kylie and Kendall stepped out in 2011 for the Kardashian Kollection Launch Party wearing black and white ensembles. While Kylie opted for a black dress with cutouts along the bodice, Kendall wore a black and white printed number. Whose look do you prefer? Be sure to vote below!

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18. Justin Bieber Never Say Never Premiere – 2011

Kendall and Kylie stepped out in 2011 for the premiere of the Justin Bieber Never Say Never film. For the occasion, the famous sisters coordinated in ruffles. While Kendall wore a peach number with ruffles along the sleeves, Kylie wore a white strapless dress with ruffles on the skirt. Whose look do you prefer?

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17. American Music Awards – 2015

Kendall and Kylie stepped out together for the American Music Awards in 2015. For the occasion, the fashionable sisters both dressed in head to toe black. Kendall opted for a black shift dress with detailing on the shoulders, which was complemented by a topknot hairstyle. Kylie, on the other hand, wore a black leather dress with silver beading and cutouts throughout. Whose look do you prefer?

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16. Kendall + Kylie Private Luncheon – 2016

In 2016, Kendall and Kylie stepped out for a private luncheon to promote their clothing line. While Kendall opted for a matching gingham set with a high ponytail, Kylie wore a simple grey dress paired with caged heels and long blonde waves. Whose look do you prefer?

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15. Kendall + Kylie Collection Event — 2016

In 2016, Kendall and Kylie stepped out for an event promoting their clothing line. While Kendall wore a white and black top paired with a wrap skirt, Kylie opted for a red cropped top paired with a fringe-style skirt. Whose look do you prefer?

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14. NBCUniversal’s Golden Globes After Party — 2017

In 2017, Kylie and Kendall stepped out in matching top knots for the NBCUniversal Golden Globes After Party. While Kendall wore a tangerine number with a thigh-high slit, Kylie wore a long sleeve metallic look with cutouts throughout. Whose look do you prefer?

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13. The Business of Fashion Dinner — 2018

In 2018 Kendall and Kylie stepped out for The Business of Fashion Dinner. While Kendall wore a plunging ivory suit paired with a red lip and coordinating heels, Kylie opted for a blue and orange printed dress which she styled with a sky-high ponytail. Whose look for the event do you prefer?

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12. Paper Towns Premiere – 2015

In 2015 Kendall and Kylie stepped out for the Paper Towns premiere in West Hollywood. While Kendall wore a billowing maroon dress with a thigh-high slit, Kylie wore a sheer champagne-colored dress paired with a suede coat and aqua wig. Whose look do you prefer? Be sure to vote below!

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11. Met Gala — 2019

Perhaps one of Kylie and Kendall’s most memorable appearance together has to the time they stepped out in coordinating ensembles for the 2019 Met Gala. While Kylie opted for a purple netted look with a feathered shawl, Kendall wore an orange look with a feathered detail around her neck and sleeve. Whose look do you prefer?

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10. Disney’s Prom Premiere – 2011

In 2011 Kendall and Kylie attended Disney’s Prom premiere rocking matching cobalt blue dresses. While Kendall wore a cotton number with cutouts on the sleeve, Kylie wore a floaty chiffon number. Whose look do you prefer?

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9. Teen Choice Awards – 2012

In 2012, Kendall and Kylie attended the Teen Choice Awards together. For the occasion, Kendall wore a little black asymmetrical dress paired with a tousled side braid, while Kylie rocked a patterned burgundy number with blue heels and long waves in her hair. Whose look do you prefer?

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8. The Hunger Games Film Premiere – 2012

The Jenner sisters both stunned at The Hunger Games premiere in 2012. While Kendall wore a patterned mini dress and a sleek updo, Kylie went with a tight white number with her hair long and straight. Whose look do you prefer?

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7. American Music Awards – 2013

For the 2013 American Music Awards, Kendall and Kylie stepped out wearing black and white ensembles. Kendall opted for a white cutout minidress with a heavy necklace and a red lip while Kylie opted for a simple white crop top and trousers which she styled with blunt bangs in her hair. Whose look do you prefer?

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6. Kendall & Kylie PacSun Launch – 2013

At the launch of their Pacsun collaboration in 2013, Kylie and Kendall stepped out rocking pieces from the collection. While Kendall wore acid wash jeans with a white lion tee, Kylie wore a blue striped matching set. Whose look do you prefer?

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5. Du Jour Magazine Cover Party – 2014

Kendall and Kylie celebrated their Du Jour cover with a party in New York City back in 2014. While Kendall wore a sheer crop top with olive green trousers, Kylie wore a black crop top with low rise trousers and a leather jacket slung over her shoulders. Which look do you prefer?

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4. Billboard Music Awards – 2014

Kendall and Kylie walked the red carpet together at the 2014 Billboard Music Awards. While Kendall wore leather pants and a white cutout bodysuit, Kylie wore a sleek white dress that allowed her teal hair to shine. Whose look do you prefer?

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3. MTV Video Music Awards – 2014

Both Kendall and Kylie opted for black ensembles at the MTV Video Music Awards in 2014. While Kendall wore a sheer top paired with black high-waisted trousers, Kylie wore a long sleeve satin dress with a thigh-high slit. Whose look do you prefer?

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2. Rebels: City of Indra Book Signing – 2014

Kendall and Kylie both looked stunning at the 2014 book signing for their novel Rebels: City Indra. While Kendall opted for a black strapless number with a polka-dotted skirt, Kylie went with a striped mini dress layered with a leather jacket. Whose look do you prefer? Be sure to vote below!

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1. Kendall and Kylie Collection Launch at Topshop – 2015

At the launch of their 2015 TopShop collection, Kendall wore a pair of black wide-leg pants paired with a striped top and caged heels, while Kylie donned a curve-hugging, burnt orange dress paired with similar caged heels. Whose look do you prefer?